반응 #1818402

반응 방정식

6-(triphenylmethylamino)-2,2-dimethyl-3-(N-[4-hydroxybenzyl]carbamoyl)penam

acetyl chloride

Phosgene

tetramethylguanidinium azide

pyridine

sodium hydroxide

→

6-(triphenylmethylamino)-2,2-dimethyl-3-(1-[4-acetoxybenzyl]tetrazol-5-yl)penam

용매

chloroform

chloroform

water

반응 조건

후처리

1. 1
   온도it is again cooled to ca. 4° C
2. 2
   기타the cooling bath is removed
3. 3
   workup.STIRRINGStirring
4. 4
   workup.WAITis continued for a further 1.5 hours
5. 5
   기타all the volatile components are removed by evaporation in vacuo
6. 6
   workup.DISSOLUTIONThe residue is redissolved in 6 ml
7. 7
   온도of chloroform and the solution is cooled to ca. 4° C. in an ice-bath
8. 8
   workup.ADDITIONTo the stirred solution is added 0.95 g
9. 9
   workup.WAITis continued for a further 1 hour at ambient temperature
10. 10
    기타The chloroform layer is separated off
11. 11
    세척washed with water
12. 12
    기타dried
13. 13
    기타evaporated to dryness in vacuo

실험 절차

To a stirred solution of 1.69 g. (3 mmole) of 6-(triphenylmethylamino)-2,2-dimethyl-3-(N-[4-hydroxybenzyl]carbamoyl)penam in 9 ml. of chloroform is added 1 ml. (12 mmole) of pyridine. The solution is cooled to ca. 4° C. in an ice-bath and 235 mg. of acetyl chloride is added slowly. The solution is stirred for 2 hours at ambient temperature, and then it is again cooled to ca. 4° C. Phosgene (1.5 ml. of a 4.3 M solution in chloroform [6.45 mmole]) is added and the cooling bath is removed. Stirring is continued for a further 1.5 hours, and then all the volatile components are removed by evaporation in vacuo. The residue is redissolved in 6 ml. of chloroform and the solution is cooled to ca. 4° C. in an ice-bath. To the stirred solution is added 0.95 g. (6 mmole) of tetramethylguanidinium azide, and then stirring is continued for a further 1 hour at ambient temperature. At this point, 25 ml. of water is added, followed by sufficient 1N sodium hydroxide to bring the pH of the aqueous phase to 10. The chloroform layer is separated off, washed with water, dried using sodium sulfate, and evaporated to dryness in vacuo. This affords crude 6-(triphenylmethylamino)-2,2-dimethyl-3-(1-[4-acetoxybenzyl]tetrazol-5-yl)penam, which is purified further by chromatography.

출처